


Always Wanted What You Couldn't Have

by Storm_cloud



Category: Supernatural
Genre: All aboard the John Winchester hate train, Bisexual Dean Winchester, But all's well that ends well, F/M, I'm really sorry I don't know how to tag shit, M/M, Not Canon Compliant, Trust me this isn't as much of a clusterfuck as the finale, a little angsty, canon? i don't know her
Language: English
Status: Completed
Published: 2020-11-30
Updated: 2020-11-30
Packaged: 2021-03-10 00:01:59
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,275
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27784927
Author URL: https://archiveofourown.org/users/Storm_cloud/pseuds/Storm_cloud
Summary: Dean Winchester's dashing looks and flirtatious smiles always establish him as a ladies man, but he has never been exclusively for the ladies, not really.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, Dean Winchester/Original Male Character(s), Dean Winchester/Other(s), Lee Webb/Dean Winchester
Comments: 4
Kudos: 71





	Always Wanted What You Couldn't Have

The first time Dean kissed a girl, he was sixteen.

When his dad left him to rot in jail, he was angry. Sad. Worried. What would Sammy do without him? Would John ever come back for a disgrace like him?

And then he found a home with Sonny, a place where he could actually be happy, a girl who understood him. It was heaven. Robin was kind and friendly, and she taught him the guitar.

Their first kiss was awkward, as teenage kisses are. Where was your tongue supposed to go? How long were you supposed to stare into each other eyes, dreaming of a future that could be?

Then John came back, and she became just that – a first kiss, a distant memory. He could never let anyone, not Robin, not Sonny, not a happy, hunter-free life keep him from being Sam’s protector. Every day of happiness at Sonny’s was undercut with a pang of guilt at leaving Sam alone with John. He could live with his own discontent, but he could never let Sammy be unhappy.

The first time Dean kissed a boy, he was seventeen.

He’d had his fair share of girlfriends and flings. A girl in every port. What was the point in falling in love if he didn’t even stay in a city for more than a month?

John had left them in Indiana for a month. They had been going to this shitty school. He’d been having make-out sessions in the supply closet with this cute blonde. He didn’t even remember her name. But she was popular, and he found himself at a party with her. Drunk on cheap beer, in a circle as a bottle spun between them. It was basically an excuse for inebriated and horny teens to make out with everyone. Dean didn’t care. Every girl here was the same to him. The bottle stopped spinning.

The way they were sitting, it should have been impossible for the bottle to point between two guys, but it happened. The mouth of the bottle facing Alex, the charismatic jock. The bottom at Dean.

“Well, let’s spin it again.” Chuckled Dean, reaching out for the bottle. A wrist gripped his. Alex’s.

“Are you chickening out, Winchester?” There was a sly smirk on his face and a snigger went through the rest of them. Dean had no choice but to return the grin.

“Oh, I’m not chicken. Are you?”

“No. So let’s do this.”

Alex leaned over, as did Dean. He only now noticed how hot Alex was, the way his blond curls fell over his grey eyes. The little scar above his upper lip. The soft curve of his mouth. His lips. Dean gulped and before anyone could notice, closed the distance between them.

The kiss was quick and chaste. Dean made a show of wiping his mouth right after, but he couldn’t get the taste out of his mouth. And he really didn’t want to. He left the party soon after, but the feelings remained. And he hated it. He tried to drive it out.

The kisses with his girlfriend were more frenzied now. He kissed more girls, other girls. It was never enough. And then he was found out. Embarrassed in front of the entire school. He was relieved beyond measure when John pulled them again for another hunt. Dean never had to see those kids again. Never had to see Alex disappearing past a row of lockers, casting a curious glance at him when he stared. Never had to blush at the sight of those lips again.

The first time Dean made love to a man, he was twenty-one.

Lee Webb was a hunter like him. John even liked him. His fighting skills were unparalleled, as were his wits. He had an easygoing aura about him, and him and Dean were fast friends. Sharing drinks and women, the pair spent most of their free time together watching old westerns and sometimes, when John was nice, he let them take the Impala and drive out.

Dean just wanted to drive into the night, windows down, jamming to some Zeppelin tunes with Lee. One night, they were parked in an empty clearing, the two of them silent while the song played in the background. Finally, Lee broke the silence. “So, your dad and Sam, huh?”

Dean fists clenched, but he sighed through gritted teeth. “Yeah. I don’t know what to do man, it’s like he keeps picking fights just to rile Dad up.”

“I don’t know man” chuckled Lee. “It don’t take a lot to piss off your old man.” The angry look from Dean quieted him. He laid a calloused hand on Dean’s shoulder and squeezed. “I’m sorry. They’ll come around, they always do.”

“Thanks.”

“It’s not your responsibility to make the both of them happy, you know. It’s theirs.”

Lee’s hand slid from Dean’s shoulder to his still-clenched fist. He was surprised, but his hand relaxed and rested comfortably in Lee’s own.

“You deserve to be happy too.” This time Dean’s bewildered eyes met Lee’s blue ones.

“Don’t look so shocked. I’ve seen you checking my ass out more than once.”

“I- I mean– I’m-”

“What, you thought I didn’t notice? Boy, you were so obvious you should have slapped my ass and taken me to the men’s bathroom.”

“You did slap my ass.” pointed out Dean.

“Well, you weren’t taking any hints so I had to be more obvious, you know.”

“Look.” Dean pulled his hand from Lee, noting the obvious hurt on the man’s face. “We can’t do this. We’re both dudes. And I like girls, not guys.”

“Ain't no one tell you could like both?”

Dean swallowed. His distress was apparent, but Lee didn’t back off.

“You look me in the eyes, Dean Winchester, and tell me you don’t want me.”

Dean’s hand gripped the front of Lee’s shirt, and for a moment it wasn’t clear if he was going to punch him or kiss him. Then he yanked him forward, closing the distance between them with his lips. His hand gripped that long, dark hair, the other slowly easing off Lee’s flannel shirt.

“Woah, there cowboy” grinned Lee as he rested a hand on Dean’s ass. “Won’t your dad mind us doing it in his car?”

For a second, Dean hesitated. Then he stripped off his t-shirt and climbed on top of Lee.

Dean’s first boyfriend was Lee.

Despite his self-acceptance, Dean wasn’t a fool to believe that his father would approve of them. They met occasionally during hunts, sharing a forbidden kiss in quiet moments and making love in motel rooms when John was away. Dean had never been with someone who understood his past, and still wanted to be with him. It wasn’t just the sex for them, and Dean found himself falling in love with the man who was there for him. Who understood the burden he carried, and was just there. And right now, Dean desperately needed someone. For once in his life, he was truly alone.

John came back to the motel one night, angry and drunk as all hell, as was custom for him ever since Sammy left for college. What he discovered was a sleeping Dean and Lee, in each other’s arms. They weren’t even naked, just cuddling on the bed, passed out after watching TV and drinking beer. If John opening the door hadn’t awoken them as it usually did, his slam certainly did.

They scrambled away from each other, but it was too late. The yells and crashing furniture nearly got the cops called on them. Lee grabbed his jacket and left. Dean didn’t stop him.

When he came back in the morning, none of them made any mention of the previous night’s events. That hunt went horribly, and the monster they were hunting killed all the kidnapped victims in a bloody massacre before it was taken down. Lee was visibly broken by their failure.

“I can’t stay here, man. All I can see are the people we let die.” He shoved his clothes into a duffel. “John will kill me if I even look at you. Or maybe he’ll kill you.”

Dean gripped his wrist sharply. Lee looked up. His eyes were brimming, but they were determined. Dean let go.

“Where are you going?” His voice was barely a whisper as he tried to hide the pain.

“Heard about a case in Texas. Maybe I’ll start there.”

“You’re going on a hunt alone?”

“Your old man don’t pull my strings no more, so I think I’m old enough for a solo hunt.” He noticed the quick anger that flared in Dean’s eyes and grasped him by the elbow. “Hey, I didn’t mean it like that. I’m sorry, Dean, but I have to go.”

He pulled the duffel onto his shoulders, then with a quick glance around, pulled Dean in for a final, lingering kiss. When he pulled back, Dean’s green eyes were looking anywhere but at him. When Lee walked off to the road to hitch a ride, Dean watched from the motel doorway. John was also watching him from the Impala, appearing to be calm on all counts but Dean could see the rage in him. He always could.

A few months later, John came upon Dean kissing a girl. He huffed and curtly told the younger Winchester “Let’s go”, but there was an almost-imperceptible sigh from him. Almost. Dean never kissed another man again. Even after John’s death, he couldn’t go past an appreciative glance or a flirty conversation with another man. Not until he met him.

The first time he met an angel, Dean was twenty-nine.

Castiel gripped him tight and raised him from perdition. So it was kind of amusing that the first thing Dean did on seeing him was to stab him. To no effect.

An angel. There were some days where he could scarce believe it. He had actually given Sam hell for believing in them a few years ago. And they were there all along. Watching over him. He was angry, at first. What did he care for heaven’s plan? They wanted to use him and Sammy to reenact the Apocalypse. Puppets in a theatre. He didn’t expect a billion year old being to understand.

But Cas did. He listened to Dean’s concerns, to his fears, to his outbursts. He quickly accepted the nickname given to him, and he began to know humanity. To Dean, this wasn’t an unknowable celestial being, he only saw a young man with spiky dark hair and blue eyes, and he treated him as such. And when he was forced to choose a side, Castiel chose Dean.

Dean saw some of himself in Castiel. A ruthless soldier with a compassionate side, for whom duty always came first. And yet, after millennia of loyalty to an absent God, Cas chose the Winchesters. Dean couldn’t abandon his father even though he’d followed him for only a fraction of that time.

Castiel was not perfect by any means. In an attempt to end Heaven’s civil war and become a better God than the one that had abandoned him, he absorbed thousands of souls from Purgatory. But he also expelled them while expressing remorse to Dean. He died, and Dean only had his trenchcoat to remember him by. He couldn’t bring himself to dispose of it. The sting of his betrayal was still there, but all he could remember when he looked at the stained trenchcoat was the quirky angel, kind of like an alien, who frightened away prostitutes and had no concept of porn plotlines. It was endearing.

When Cas came back from the dead and regained his memories, Dean couldn’t bring himself to hate him. In every fucked-up circumstance, all Cas wanted to do was help them. Even when they were in Purgatory, fighting for their lives, Cas led the monsters away from him. Dean didn’t care. Castiel was his best friend and the only person he loved as much as Sam.

The comments antagonistic angels and demons made on their relationship did not escape his notice. Hah. Fat chance of that happening. Castiel was an angel. A being for whom eternity passed in a blink of an eye. Who still had no idea what Scooby Doo was, or why humans made small talk. So even if he had made out with a demon or had sex with a reaper, he wouldn’t understand the concept of romantic love. It wasn’t that Dean was really against the idea, it was just that it was impossible, and what was the point in hoping for something that could never be?

Dean had tried, Dean had hinted, but it was evident from the replies that Cas saw him as a friend, his first friends. So maybe his social skills were not up to par, but Dean was comfortable, he was happy if Cas was content to be his friend. He sure as hell did not have many of those still around.

So when Cas stood in the bunker and confessed his love to him, while Death herself banged on the door, Dean was speechless to say the least. He couldn’t get one word out while this man spouted out praise after praise for him, also choosing that exact moment to reveal that he was going to the Empty the second he confessed. And then Cas said it.

“I love you.”

How was he supposed to process all of this? His best friend, the man he loved, had loved for a long time but resigned to a friendship, loved him back, and now was going to die for it.

“I love you too, Cas.” The words came out choked, the tears flowing quickly. Why did it have to be this way? Why did it always have to be this way? How could have not known that Cas loved him too? How could he have lived a decade with this man and never known their true feelings for each other?

The manifestation of the Empty appeared behind him, and Dean reached for Cas. He wasn’t going to let him be taken, he had lost far too many people to lose Cas too.

But the angel gripped his shoulder, tears streaming down his face, and shoved Dean away. In the few minutes of shock, the mere seconds as the Empty grabbed Castiel and Death, and disappeared, all Dean could think was

“He loved me. He’s gone because of me.”

After Chuck was defeated and Jack took his place, Dean tried. He prayed to Jack privately, begged him. But the Empty was adamant and angry. Castiel was its prisoner. Dean wallowed in misery and drink for a few days. He tried to put up a false pretense for Sam, who was happy with Eileen. He didn’t want to ruin that. But when he saw them, he couldn’t help but feel a little jealous. He could’ve had that with Cas.

One night he was thumbing through his phone’s gallery with photos of Cas, with a heavy Men of Letters tome on the Empty on the other side of the bed. Sam knocked at the doorframe.

“You okay?”

“Why wouldn’t I be?” he smiled cheerily. “We defeated Chuck, everyone’s back. I even have a dog.” Dean gave a quick whistle and Miracle leapt onto his bed, sending papers flying everywhere and knocking the phone from Dean’s hand.

Sam sighed. “You know that not everyone’s back. You don’t have to pretend to be happy with me, Dean. I miss him too.” He cast a glance at the phone, showing a picture of the three of them – Sam, Dean and Cas, smiling politely for the camera. What Dean remembered with a wistful smile was how Sam and Cas had surprised him for his birthday right after, whipping out a pie that thankfully wasn’t smashed into Dean’s face.

“You don’t understand, Sammy.” The mask was off now. “The Empty took him because of me. He did it to save me. When he- he told me that-” Dean couldn’t bring himself to say it.

“That he loved you?”

Dean’s teary eyes looked up in shock.

“Yeah, I’ve kinda known. You’re not really subtle about it. And Cas is the opposite of subtle.”

“He was happy when he said it. And that’s why the Empty took him. Because he was happy.”

“I’m sorry, Dean.”

“Yeah well, sorry ain’t gonna help him.” He wiped his tears on his sleeve. “I need to get out.”

“Dean-”

“I just need some air.” He grabbed his jacket and slammed the door on the way out. When he got in Baby and drove, he wasn’t even looking where he was going. Just driving on the long open road. He reached into the glovebox for a tape. He grabbed the first one and read it out.

“Dean’s Top 13 Zepp Traxx”.

Why did everything have to be a reminder of him? He considered chucking it out the window, but couldn’t bring himself to do it. He couldn’t lose that too. He popped it into the deck. He let the songs to carry him away as he just drove on and on.

He wasn’t surprised when day broke and he found himself in a barn. Specifically, the barn where they first met Cas. He could still see him walking in, lights exploding with every step, taking a shotgun blast with barely a flinch. What a drama queen, thought Dean, and he realised he was crying again. He let the tears come. Who would see him here?

“Hello Dean.”

The words were familiar, the voice even more. Dean whirled around.

“Cas?”

The figure was unmistakable – a bit tired, maybe, but that was Cas all right. Dean couldn’t feel his feet walking, but he was in front of the angel in a second and slamming him in a bear hug, nearly crushing him. But he let go the same instant, hesitant.

“How do I know you’re…”

Cas held out his hands. He understood.

Dean splashed a bit of holy water and did the silver test. No burns. It was the real Cas.

“How did you get out?” Dean didn’t know if he was dreaming. If he was, he wished he’d never wake up.

“The Empty wanted to keep me forever, to punish me. But it could only keep angels, and well, I’m no longer an angel.”

“You- you’re human?”

Cas smiled. “I’ve been losing my power for some time. I don’t know why. By the time the Empty took me, I was nearly human. It held on to me for as long as it could, but in the end, it threw me out.”

“Cas, I didn’t know, I’m so sorry.”

“It’s all right Dean, you were dealing with Chuck and-”

“No it isn’t!” Dean exploded. “You’ve been in love with me this whole time and I never knew. You were here for me and I was mad at you for something that wasn’t even your fault. If I’d told you sooner, you wouldn’t have gone to the Empty in the first place.”

Cas held both of Dean’s hands in his own, caressing them. Bringing the tirade to an end. Calming the stormy sea that was Dean Winchester’s emotions. “I forgive you.”

Dean slowly freed his hands and let them rest on either side of Castiel’s face. Let his thumb graze across the grainy stubble. Gripped that shock of dark hair and kissed him. Let his arms wrap tight around his love and hold him as close as he could, and never let go.

The first time Dean kissed the love of his life, he was forty-one.

**Author's Note:**

> First fic that I ever published, but this has been rattling in my head ever since I saw 15x07, and then the finale happened. So...  
> Despite the CW's insistence that Dean is straight and the dangerously gay/pan angel won't see him again(open ending my ass) there are tons of videos on YouTube, not about Destiel moments, but with Bi!Dean, because no matter how hard you deny, the man loves both boys and girls(We will always have "Y yo a ti, Cas")


End file.
